ChemSpider 2D Image | Talarozole | C21H23N5S

Talarozole

  • Molecular FormulaC21H23N5S
  • Average mass377.506 Da
  • Monoisotopic mass377.167419 Da
  • ChemSpider ID7975653

More details:






Validated by Experts, Validated by Users, Non-Validated, Removed by Users

201410-53-9 [RN]
2-Benzothiazolamine, N-[4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl]- [ACD/Index Name]
N-{4-[2-ethyl-1-(1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amine
N-{4-[2-Ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amin [German] [ACD/IUPAC Name]
N-{4-[2-Ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl}-1,3-benzothiazol-2-amine [ACD/IUPAC Name]
N-{4-[2-Éthyl-1-(1H-1,2,4-triazol-1-yl)butyl]phényl}-1,3-benzothiazol-2-amine [French] [ACD/IUPAC Name]
Rambazole [Trade name]
talarozol [Spanish] [INN]
talarozole [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

8964 [DBID]
R115866 [DBID]
1BCQ2C7O9W [DBID]
3R07P85RNH [DBID]
R 115866 [DBID]
R-115866 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A member of the class of benzothiazoles that is 2-amino-1,3-benzothiazole in which one of the amino hydrogens is replaced by a 4-[2-ethyl-1-(1<element>H</element>-1,2,4-triazol-1-yl)butyl]phenyl group . ChEBI CHEBI:102167
      A member of the class of benzothiazoles that is 2-amino-1,3-benzothiazole in which one of the amino hydrogens is replaced by a 4-[2-ethyl-1-(1H-1,2,4-triazol-1-yl)butyl]phenyl group. ChEBI CHEBI:102167
    • Bio Activity:

      Cytochrome P450 MedChem Express HY-14531
      Metabolism/Protease MedChem Express HY-14531
      Metabolism/Protease; MedChem Express HY-14531
      Talarozole(R115866) is a potent and selective inhibitor of cytochrome P450 26-mediated breakdown of endogenous all-trans retinoic acid for the treatment of psoriasis and acne.; IC50 Value: ; Target: CYP26; in vitro: Talarozole treatment increased the mRNA expression of CRABP2, KRT4, CYP26A1 and CYP26B1 dose dependently, and decreased theexpression of KRT2 and IL-1alpha compared with vehicle-treated skin. MedChem Express HY-14531
      Talarozole(R115866) is a potent and selective inhibitor of cytochrome P450 26-mediated breakdown of endogenous all-trans retinoic acid for the treatment of psoriasis and acne.;IC50 Value: ;Target: CYP26;In vitro: Talarozole treatment increased the mRNA expression of CRABP2, KRT4, CYP26A1 and CYP26B1 dose dependently, and decreased theexpression of KRT2 and IL-1alpha compared with vehicle-treated skin. No mRNA change in retinol-metabolizing enzymes was obtained. There was no induction of epidermal thickness or overt skin inflammation in talarozole-treated skin. Immunofluorescence analysis confirmed an upregulation of KRT4 protein, but no upregulation of CYP26A1 and CYP26B1 expression was detected [1] [2].;In vivo: Talarozole slightly diffused into the skin only when dissolved in propylene glycol, isopropyl myristate or ethanol. Although only 0.1% of the dose applied was found in the skin itself after 12-24 h, this was sufficient to achieve local concentrations well above the half-m MedChem Express HY-14531

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point: 561.0±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.4±3.0 kJ/mol
Flash Point: 293.1±32.9 °C
Index of Refraction: 1.678
Molar Refractivity: 112.7±0.5 cm3
#H bond acceptors: 5
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 1
ACD/LogP: 5.16
ACD/LogD (pH 5.5): 4.76
ACD/BCF (pH 5.5): 2459.93
ACD/KOC (pH 5.5): 9295.53
ACD/LogD (pH 7.4): 4.77
ACD/BCF (pH 7.4): 2470.66
ACD/KOC (pH 7.4): 9336.08
Polar Surface Area: 84 Å2
Polarizability: 44.7±0.5 10-24cm3
Surface Tension: 49.7±7.0 dyne/cm
Molar Volume: 298.9±7.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  6.03

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  515.76  (Adapted Stein & Brown method)
    Melting Pt (deg C):  219.96  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  9.04E-011  (Modified Grain method)
    Subcooled liquid VP: 1.09E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  0.03007
       log Kow used: 6.03 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.33468 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.47E-013  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.493E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.03  (KowWin est)
  Log Kaw used:  -11.221  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.251
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3341
   Biowin2 (Non-Linear Model)     :   0.0139
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2300  (months      )
   Biowin4 (Primary Survey Model) :   3.1947  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.4472
   Biowin6 (MITI Non-Linear Model):   0.0007
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6360
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.45E-006 Pa (1.09E-008 mm Hg)
  Log Koa (Koawin est  ): 17.251
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.06 
       Octanol/air (Koa) model:  4.38E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.987 
       Mackay model           :  0.994 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 385.0884 E-12 cm3/molecule-sec
      Half-Life =     0.028 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    19.998 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.99 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  8.078E+006
      Log Koc:  6.907 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 3.940 (BCF = 8715)
       log Kow used: 6.03 (estimated)

 Volatilization from Water:
    Henry LC:  1.47E-013 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.739E+009  hours   (3.224E+008 days)
    Half-Life from Model Lake : 8.442E+010  hours   (3.518E+009 days)

 Removal In Wastewater Treatment:
    Total removal:              92.28  percent
    Total biodegradation:        0.77  percent
    Total sludge adsorption:    91.51  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       4.48e-005       0.667        1000       
   Water     2.33            1.44e+003    1000       
   Soil      49.8            2.88e+003    1000       
   Sediment  47.9            1.3e+004     0          
     Persistence Time: 5.26e+003 hr




                    

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